The Ledger

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why aren't all 26 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Insight
Shah: Forcing Haystack to lead every deal lowers portfolio quality
“If we tried to lead everything, we would lower the I think the quality of the portfolio that we're in.”
Semil Shah Nov 21, 2022 ▶ 17:24 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Insight
Shah: Scaling seed funds to $100M+ breaks collaborative syndicate dynamics
“If I had a hundred, fifty million dollar fund, that whole collaboration layer of how we work would change, which would then set off a chain reaction of how the deal flow would change and how we would have to operate with the companies would change.”
Semil Shah Nov 21, 2022 ▶ 18:56 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Disclosure
Shah: I blocked two LPs from re-investing in future Haystack funds
“I've blocked two LPs from investing in, in future funds.”
Semil Shah Nov 21, 2022 ▶ 46:02 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Prediction Held up
Shah: Future Haystack funds will remain capped under $100 million
“Our next funds, by the way, will modestly grow, but I still think, you know, for what we do, it's gotta be under a hundred million dollars.”
Semil Shah Nov 21, 2022 ▶ 4:27 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Insight
Shah: Early venture outcomes are random, making price discipline critical
“When we all invest so early, the outcomes are completely random, they're completely unknown, and so we have to kind of take a cohort basis. And what you have now is especially in the Bay Area, such a free flow of capital and a loosening of norms around how fun…”
Semil Shah Sep 16, 2019 ▶ 37:00 20VC: Haystack's Semil Shah on Whether Founders Are Bypassing Seed Funds in Favour Of Less Dilutive Multi-Stage Funds, How Fund Strategy Changes With Fund Scaling & Why The Hardest Challenge is Price Discipline
Disclosure
Shah: Haystack turned a $25k check in HashiCorp into $30M–$35M
“I think it was like the 25 K turned into something like 30, thirty five million bucks.”
Semil Shah Nov 21, 2022 ▶ 1:18:24 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Disclosure
Shah: Haystack missed fundraising targets for its first four funds
“Well, remember the first four, I was never able to reach the target of what We wanted to raise. So there were always underwhelming in that sense”
Semil Shah Nov 21, 2022 ▶ 3:13 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Disclosure
Haystack stopped announcing deals to shield founders from downstream VCs
“I decided in fund four, Harry, we don't really announce the investments, and it's an interesting topic. What happened in the first three funds is, I think, partly because we were successful in finding good companies early, and there was a good rate of series A…”
Semil Shah Sep 16, 2019 ▶ 38:19 20VC: Haystack's Semil Shah on Whether Founders Are Bypassing Seed Funds in Favour Of Less Dilutive Multi-Stage Funds, How Fund Strategy Changes With Fund Scaling & Why The Hardest Challenge is Price Discipline
Insight
Venture funds over $40 million must strictly focus on ownership
“I'm sort of the paranoid belief that in any vehicle, if you have over forty million dollars, you have to be so laser focused on ownership, regardless of how many GPs you have, in order to have a really good fund.”
Semil Shah Oct 23, 2017 ▶ 19:00 20VC: Semil Shah on How To Raise An Institutional Venture Fund, Why LPs Mostly Have Reserve Allocation Theory Wrong & Why IPOs and Acquisitions Are Severely Constrained
Insight
Semil Shah: Abundant Capital Shifted Seed Fundraising to a Relationship Game
“There's so much money in seed that the boiling point is that it goes from becoming a market-based game to a relationship game, and a lot of people can't make that transition.”
Semil Shah Jul 25, 2016 ▶ 10:54 20VC: Semil Shah on Why The Most Important Thing An Investor Can Do Is Attract Follow On & The Fundamentals of VC Branding
Disclosure
Semil Shah Failed to Reach His Target Goal for Every Haystack Fund
“I've been unsuccessful in raising my target for every fund.”
Semil Shah Jul 25, 2016 ▶ 5:00 20VC: Semil Shah on Why The Most Important Thing An Investor Can Do Is Attract Follow On & The Fundamentals of VC Branding
Disclosure
Shah: Haystack sets initial ownership floor at 5%
“I would say we stop around five percent. So if you look, yeah. So if you look at like what we tell the entrepreneur is like, look, we're trying to own five and 10% to start. We want to earn the right to maintain that over a few rounds, right? And we'll never o…”
Semil Shah Nov 21, 2022 ▶ 19:47 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Disclosure
Shah: Haystack operates on a 24-to-30-month fund deployment cycle
“What I kind of concluded over that time and what I told our LPs is that for the seed market I felt like the thing we could promise is 24 to 30 month deployments. And then doing, doing new, new funds. And I would say that since we last spoke, I would say it's c…”
Semil Shah Nov 21, 2022 ▶ 22:26 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Assertion Supported
Shah: Pre-seed startup round sizes doubled over the last decade
“Over the last 10 years, just simply because of inflation, those are all doubled, you know?”
Semil Shah Nov 21, 2022 ▶ 5:06 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Disclosure
Haystack scaled check sizes from $25K in Fund I to $500K
“Fund one was 25 K checks, Fund two was 50 and a hundred K checks with a couple of 200. Fund three was a hundred to two 50 K checks with a couple of six, four to 600 checks. And then fund four, which we're just closing up has been around 500 K checks, give or t…”
Semil Shah Sep 16, 2019 ▶ 22:14 20VC: Haystack's Semil Shah on Whether Founders Are Bypassing Seed Funds in Favour Of Less Dilutive Multi-Stage Funds, How Fund Strategy Changes With Fund Scaling & Why The Hardest Challenge is Price Discipline
Prediction Partly held up
Shah: Haystack Fund V will deploy $50M over at least three years
“Disclosed fund five a few months ago. We haven't opened it yet. It's going to be a fifty million dollar vehicle. You know, I told everyone, and I hope you can hold me accountable to this, Harry. You know, it'll be at least a three-year fund”
Semil Shah Sep 16, 2019 ▶ 18:48 20VC: Haystack's Semil Shah on Whether Founders Are Bypassing Seed Funds in Favour Of Less Dilutive Multi-Stage Funds, How Fund Strategy Changes With Fund Scaling & Why The Hardest Challenge is Price Discipline
Opinion
Mignano: Haystack is a top seed fund with generational outcomes
“Second answer, I would say tied for, you know, my favorite seed fund has gotta be Haystack. I'm just a huge fan of Samil and Divya and the work they do. It's an incredible fund. Obviously, they've produced some generational outcomes.”
Mike Mignano Jul 6, 2026 ▶ 1:04:15 Why Now is the Time for the App Layer | Why Startups Should be TokenMaxxing | Mike Mignano, USV · 20VC with Harry Stebbings
Disclosure
Shah: Haystack achieved nearly 7% initial ownership in recent funds
“We've been able to get close to seven percent initial entry ownership in the last two funds.”
Semil Shah Nov 21, 2022 ▶ 6:01 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Disclosure
Shah: Haystack maintains a standard 2-and-20 fee structure across all funds
“And so I think Fred has been on the record of just saying like, they just, you know, do a standard two and 20 on every fund. So I haven't really Seeing the need to deviate from that.”
Semil Shah Nov 21, 2022 ▶ 41:42 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Disclosure
Shah: Haystack led only about 10 deals over three years
“If you look over the last three years we've maybe led, you know, 10 deals. Ten-ish.”
Semil Shah Nov 21, 2022 ▶ 15:34 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Disclosure
Shah: Haystack's 10-year deal valuations clustered between $8M and $15M
“If you look at the activity of all the deals over, over 10 years, I would say there's like a tight clustering between eight and fifteen million dollars as the entry point and the rounds being, you know, three million dollars or less.”
Semil Shah Nov 21, 2022 ▶ 6:12 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Disclosure
Shah: Haystack Fund 4 holds 5%-10% stakes in potential IPO candidates
“So the good thing about all of this is that we have like five to 10% positions in, in three or four, like really amazing companies that all could be public actually at some point.”
Semil Shah Nov 21, 2022 ▶ 25:17 Semil Shah: Lessons Learned Scaling from a $1M to a $50M Fund | 20VC #951 · 20VC with Harry Stebbings
Disclosure
Haystack's early funds relied on $10,000 to $25,000 checks
“When I raised my first, second fund, I just went to people I knew, like founders I've backed, VCs that I worked for, and would literally be collecting 10 K checks, 25 K checks. You know, still took some 10 K checks on this fund from people I know.”
Semil Shah Oct 23, 2017 ▶ 21:38 20VC: Semil Shah on How To Raise An Institutional Venture Fund, Why LPs Mostly Have Reserve Allocation Theory Wrong & Why IPOs and Acquisitions Are Severely Constrained
Disclosure
Semil Shah Targeted $5M for Haystack Fund I But Raised $1M
“I tried to raise five, and I could only raise one.”
Semil Shah Jul 25, 2016 ▶ 4:22 20VC: Semil Shah on Why The Most Important Thing An Investor Can Do Is Attract Follow On & The Fundamentals of VC Branding
Disclosure
Shah launched Haystack with initial funds of $1M and $3.2M
“And what happened was, is that I loved doing those initial small funds. They were just very small, one million dollars, 3.2 million dollars.”
Semil Shah Sep 16, 2019 ▶ 5:13 20VC: Haystack's Semil Shah on Whether Founders Are Bypassing Seed Funds in Favour Of Less Dilutive Multi-Stage Funds, How Fund Strategy Changes With Fund Scaling & Why The Hardest Challenge is Price Discipline
Disclosure
Semil Shah Maintains a Core Network of 80 Investors for Co-Investments
“I keep a very tight network of about 80 seed investors, angels that I know, larger VCs, and kind of executives at companies that I've all Invested with in some way or worked with in some way, and if there's ever room in any of the companies that I'm investing …”
Semil Shah Jul 25, 2016 ▶ 11:38 20VC: Semil Shah on Why The Most Important Thing An Investor Can Do Is Attract Follow On & The Fundamentals of VC Branding
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